Criteria for the elucidation of the pseudopericyclic character of the cyclization of (Z)-1,2,4,6-heptatetraene and its heterosubstituted analogues: Magnetic properties and natural bond orbital analysis

Chemistry - A European Journal

Volumn 9, Issue 8, 2003, Pages 1837-1843

  Rodríguez Otero, Jesús ^a   Cabaleiro Lago, Enrique M ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b Universidad de Santiago da Compostela   (Spain)

Author keywords

Ab initio calculations; Aromaticity; Density functional calculations; Electrocyclic reactions; Transition states

Indexed keywords

DERIVATIVES; ELECTRONS; MAGNETIC PROPERTIES;

ELECTROCYCLIZATION;

ORGANIC COMPOUNDS;

1,2,4,6 HEPTATETRAENE DERIVATIVE; 2,4,5 HEXATRIEN 1 IMINE DERIVATIVE; 2,4,5 HEXATRIENAL DERIVATIVE; AROMATIC COMPOUND; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ANISOTROPY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DENSITY FUNCTIONAL THEORY CALCULATION; ENERGY; GEOMETRY; MAGNETIC FIELD;

EID: 0038523834     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390211     Document Type: Article

References (52)

1. J. A. Ross, R. P. Seiders, D. M. Lemal, J. Am. Chem. Soc. 1976, 98, 4325.
2. C. H. Bushweller, J. A. Ross, D. M. Lemal, J. Am. Chem. Soc. 1977, 99, 629.
3. D. M. Birney, P. E. Wagenseller, J. Am. Chem. Soc. 1994, 116, 6262.
4. S. Ham, D. M. Birney, Tetrahedron Lett. 1994, 35, 8113.
5. P. E. Wagenseller, D. M. Birney, D. Roy, J. Org. Chem. 1995, 60, 2853.
6. D. M. Birney, J. Org. Chem. 1996, 61, 243.
7. D. M. Birney, S. Ham, G. R. Unruh, J. Am. Chem. Soc. 1997, 119, 4509.
8. D. M. Birney, X. Xu, S. Ham, Angew. Chem. 1999, 111, 147; Angew. Chem. Int. Ed. 1999, 38, 189.
9. D. M. Birney, X. Xu, S. Ham, Angew. Chem. 1999, 111, 147; Angew. Chem. Int. Ed. 1999, 38, 189.
10. D. M. Birney, J. Am. Chem. Soc. 2000, 122, 10917.
11. W. Shumway, S. Ham, J. Moer, B. R. Whittlesey, D. M. Birney, J. Org. Chem. 2000, 65, 7731.
12. W. W. Shumway, N. K. Dalley, D. M. Birney, J. Org. Chem. 2001, 66, 5832.
13. C. Zhou, D. M. Birney, J. Am. Chem. Soc. 2002, 124, 5231.
14. W. M. F. Fabian, V. A. Bakulev, C. O. Kappe, J. Org. Chem. 1998, 63, 5801.
15. W. M. F. Fabian, C. O. Kappe, V. A. Bakulev, J. Org. Chem. 2000, 65, 47.
16. L. Luo, M. D. Bartberger, W. R. J. Dolbier, J. Am. Chem. Soc. 1997, 119, 12366.
17. G. Rauhut, J. Org. Chem. 2001, 66, 5444.
18. M. Alajarin, A. Vidal, P. Sanchez-Andrada, F. Tovar, G. Ochoa, Org. Lett. 2000, 2, 965.
19. A. R. de Lera, R. Alvarez, B. Lecea, A. Torrado, F. P. Cossio, Angew. Chem. 2001, 113, 570; Angew. Chem. Int. Ed. 2001, 40, 557.
20. A. R. de Lera, R. Alvarez, B. Lecea, A. Torrado, F. P. Cossio, Angew. Chem. 2001, 113, 570; Angew. Chem. Int. Ed. 2001, 40, 557.
21. J. Rodríguez-Otero, E. M. Cabaleiro-Lago, Angew. Chem. 2002, 114, 1195; Angew. Chem. Int. Ed. 2002, 41, 1147.
22. J. Rodríguez-Otero, E. M. Cabaleiro-Lago, Angew. Chem. 2002, 114, 1195; Angew. Chem. Int. Ed. 2002, 41, 1147.
23. H. E. Zimmerman, Acc. Chem. Res. 1971, 4, 272.
24. R. Herges, H. Jiao, P. v. R. Schleyer, Angew. Chem. 1994, 106, 1441; Angew. Chem. Int. Engl. Ed. 1994, 33, 1376.
25. R. Herges, H. Jiao, P. v. R. Schleyer, Angew. Chem. 1994, 106, 1441; Angew. Chem. Int. Engl. Ed. 1994, 33, 1376.
26. H. Jiao, P. v. R. Schleyer, J. Org. Phys. Chem. 1998, 11, 655.
27. M. Manoharan, F. De Proft, P. Geerlings, J. Org. Chem. 2000, 65, 7971.
28. M. Manoharan, F. De Proft, P. Geerlings, J. Chem. Soc. Perkin Trans. 2 2000, 1767.
29. P. v. R. Schleyer, H. Jiao, Pure Appl. Chem. 1996, 68, 209.
30. See special Issue 5 entirely dedicated to aromaticity, Chem. Rev. 2001, 101.
31. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. v. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317.
32. J. P. Foster, F. Weinhold, J. Am. Chem. Soc. 1980, 102, 7211.
33. A. D. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
34. E. D. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold, NBO 3.1 Program Manual, 1988.
35. A. R. de Lera, F. P. Cossio, Angew. Chem. 2002, 114, 1198; Angew. Chem. Int. Ed. 2002, 41, 1150.
36. A. R. de Lera, F. P. Cossio, Angew. Chem. 2002, 114, 1198; Angew. Chem. Int. Ed. 2002, 41, 1150.
37. Gaussian 98 (Revision A.9), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
38. C. Lee, W. Yang, R. J. Parr, Phys. Rev. B 1988, 37, 785.
39. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
40. J. Rodriguez-Otero, J. Org. Chem. 1999, 64, 6842.
41. K. Fukui, Acc. Chem. Res. 1981, 14, 363.
42. C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154.
43. C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5223.
44. K. Wolinski, J. F. Hilton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251.
45. T. A. Keith, R. F. W. Bader, Chem. Phys. Lett. 1993, 210, 223.
46. T. A. Keith, R. F. W. Bader, Chem. Phys. Lett. 1992, 194, 1.
47. J. R. Cheeseman, M. J. Frisch, G. W. Trucks, T. A. Keith, J. Chem. Phys. 1996, 104, 5497.
48. A. P Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502.
49. F. Cossio, I. Morao, P. v. R. Schleyer, H. Jiao, J. Am. Chem. Soc. 1999, 121, 6737.
50. R. F. W. Bader, Atoms in molecules. A quantum theory, Clarendon Press, Oxford, 1990.
51. R. F. W. Bader, and co-workers, AIMPAC: A suite of programs for the Theory of Atoms in Molecules. Contact bader@mcmail.cis.mcmaster.ca, Hamilton, Ontario (Canada).
52. M. J. Walker, B. N. Hietbrink, B. E. Thomas IV, K. Nakamura, E. A. Kallel, K. N. Houk, J. Org. Chem. 2001, 66, 6669.